Nucleophile- or light-induced synthesis of 3-substituted phthalides from 2-formylarylketones

Article

Authorship:

GERBINO, DARIO CESAR ; Augner, Daniel ; Slavov, Nikolay ; Schmalz, Hans Günther

Date:

2012

Publishing House and Editing Place:

American Chemical Society

Magazine:

ORGANIC LETTERS, vol. 14 (pp. 2338-2341) American Chemical Society

Summary

The surprisingly facile conversion (isomerization) of 2-formyl-arylketones into 3-substituted phthalides, as observed for the marine natural product pestalone and its per-O-methylated derivative, was investigated using a series of simple 2-acylbenzaldehydes as substrates. The transformation generally proceeds smoothly in DMSO, either in a Cannizarro-Tishchenko-type reaction under nucleophile catalysis (NaCN) or under photochemical conditions (DMSO, 350 nm). © 2012 American Chemical Society.

Key Words

Phthalides2-FormylarylketonesPestaloneCannizarro-Tishchenko-type reaction

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http://hdl.handle.net/11336/63935